An investigation into the synthesis and pharmaceutical applications of trans-dibenzalacetone and a few of its simple derivatives
Assignment #2
The Aldol Condensation: A Simple Teaching Model for Organic Laboratory DOI
#1: Experiments using an aldol condensation typically do not have a defined educational goal and so this experiment was designed to teach students many important organic chemistry concepts, while being able to be completed within the time allotted (3 hours).
#2: A molecule without an alpha-hydrogen cannot undergo self-condensation, but can participate in cross-condensation with the carbanion formed from another molecule, such as acetone. This experiment examines the result of reacting benzaldehyde and acetone at different relative concentrations to obtain dibenzalacetone and benzalacetone.
#3: The products obtained by the reactions must be isolated and identified to validate the reactions and provide practice in identifying impure product that is in oil form (benzalacetone) by reacting with another compound and confirming by measuring the melting point.
#4: To form dibenzalacetone, an ethanol solution with benzaldehyde is mixed with an aqueous NaOH solution and then acetone is added to the solution. The benzaldehyde is in excess and the dibenzalacetone crystals that form are removed by vacuum filtration and purified by recrystallization from ethanol with water used to promote crystal formation.
#5: To form benzalacetone, an ethanol solution with benzaldehyde is mixed with aqueous NaOH and acetone is added in excess. Unreacted benzaldehyde is removed by oxidation using a 3% hydrogen peroxide solution.
#6: The benzalacetone product is extracted using ether, dried on magnesium sulfate and evaporated to an oil.
#7: To convert the benzalacetone product to a 2,4-dinitrophenylhydrazone derivative, a 2,4-dinitrophenylhydrazine reagent is created by mixing a 2,4-dinitrophenylhydrazine in concentrated sulfuric acid solution with an aqueous carbonyl free ethanol solution and filtering.
#8: The benzalacetone oil is dissolved in ethanol and mixed with the 2,4-dinitrophenylhydrazine reagent to form crystals. The recovered crystals are boiled in ethanol and once dry, the melting point of the 2,4-dinitrophenylhydrazone derivative crystals are measured.
#9: Each product can also be characterized using spectroscopic methods.
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Research Topic
An investigation into the synthesis and pharmaceutical applications of trans-dibenzalacetone and a few of its simple derivativesAssignment #2
The Aldol Condensation: A Simple Teaching Model for Organic LaboratoryDOI
#1: Experiments using an aldol condensation typically do not have a defined educational goal and so this experiment was designed to teach students many important organic chemistry concepts, while being able to be completed within the time allotted (3 hours).
#2: A molecule without an alpha-hydrogen cannot undergo self-condensation, but can participate in cross-condensation with the carbanion formed from another molecule, such as acetone. This experiment examines the result of reacting benzaldehyde and acetone at different relative concentrations to obtain dibenzalacetone and benzalacetone.
#3: The products obtained by the reactions must be isolated and identified to validate the reactions and provide practice in identifying impure product that is in oil form (benzalacetone) by reacting with another compound and confirming by measuring the melting point.
#4: To form dibenzalacetone, an ethanol solution with benzaldehyde is mixed with an aqueous NaOH solution and then acetone is added to the solution. The benzaldehyde is in excess and the dibenzalacetone crystals that form are removed by vacuum filtration and purified by recrystallization from ethanol with water used to promote crystal formation.
#5: To form benzalacetone, an ethanol solution with benzaldehyde is mixed with aqueous NaOH and acetone is added in excess. Unreacted benzaldehyde is removed by oxidation using a 3% hydrogen peroxide solution.
#6: The benzalacetone product is extracted using ether, dried on magnesium sulfate and evaporated to an oil.
#7: To convert the benzalacetone product to a 2,4-dinitrophenylhydrazone derivative, a 2,4-dinitrophenylhydrazine reagent is created by mixing a 2,4-dinitrophenylhydrazine in concentrated sulfuric acid solution with an aqueous carbonyl free ethanol solution and filtering.
#8: The benzalacetone oil is dissolved in ethanol and mixed with the 2,4-dinitrophenylhydrazine reagent to form crystals. The recovered crystals are boiled in ethanol and once dry, the melting point of the 2,4-dinitrophenylhydrazone derivative crystals are measured.
#9: Each product can also be characterized using spectroscopic methods.